Reality Bites wasn't the first slacker movie, or maybe even the best one. But the unconventional aesthetic surrounding Ben Stiller's directorial debut was perfectly matched with its soundtrack – and the result was one of Generation X's best romantic comedies.

"The soundtrack was a curated mix tape that was a souvenir of the movie," producer Stacey Sher told Uproxx in 2014. "Kathy Nelson at Universal was a big believer – even though she ended up not doing the record with us – in this notion of souvenirs of the film for an audience."

RCA opened their artist roster for the film, after meeting with Stiller and music supervisor Karyn Rachtman three weeks into filming. The label in turn aggressively marketed the soundtrack, ultimately placing five songs in radio rotations and on MTV.

The video for Crowded House's "Locked Out" was re-edited to include scenes from Reality Bites, and Stiller also directed the clip for the Juliana Hatfield Three's "Spin the Bottle." Elsewhere, the soundtrack included a deft mix of songs both old (Squeeze's "Tempted," U2's "All I Want Is You") and relatively new, like Dinosaur Jr.'s wonderfully angsty "Turnip Farm." (In a moment of modern irony, they also referenced "Conjunction Junction" from Schoolhouse Rock!)

"Being in your early 20s isn't a happy time," Hawke told the Guardian in 2018. "Everybody is so hungry to prove themselves, even to themselves." Sometimes, you just left dancing like a goofball, right there in a gas station, to the Knack's "My Sharona."

The movie's breakout musical star, however, became the previously unknown Lisa Loeb. Hawke was her friend and neighbor. He introduced her to Stiller then later directed the music video for "Stay (I Missed You)," a No. 1 smash. "She recorded that song, 'Stay,' and I thought, 'Man,"" Hawke told Uproxx. "I sent it to Ben because when I heard it I just really felt like it was so perfect for the film. And he completely agreed."

Sher and Stiller were in New York City, planning to catch a late flight to Dublin to get permission from U2 to use "All I Want Is You" when they got word that the band had given the early go-ahead. So, they decided to attend a theater-company benefit where Loeb was playing. That cinched it.

"We hung out together, supported each other, and so at the time it seemed totally normal and natural that Ethan might ask for a song," Loeb told Uproxx. "It was exciting, of course, but in retrospect it's much more surprising. Now, I realize that even if you have friends who are actors and making movies or other people in your life who might be able to connect you with an incredible opportunity, it usually doesn't happen. And even when it does happen, it doesn't necessarily follow through to such great success."

Watch Lisa Loeb Perform 'Stay (I Missed You)'

Ryder's character Lelaina Pierce lives a life that's not that uncommon for struggling artist-types, as she exits school hoping to become a serious documentarian only to end up working for a crass cable-TV company. "The backdrop of the movie is a world where you go to college and you think, if you do well, there'll be a job out there waiting for you," Stiller told the Baltimore Sun in 1994. "That's not the way the world is anymore."

Lelaina tries filming her own life, and that provides the movie's episodic insights – but also its reality-show twist. Youthful idealism seems to evaporate with each passing frame, and the songs echo everything. ("I was valedictorian!" Lelaina cries, while turning down a minimum-wage job.) That said, it's clear that the filmmakers weren't trying to define a generation. Reality Bites, which opened on Feb. 18, 1994, was actually just a determinedly small-scale rom-com with a couple of new twists. In fact, the characters seem to find the most comfort in old-fashioned things like simple conversation, 7-11 Big Gulps, and the utterly un-grungy Frampton Comes Alive.

"I made [the movie] for a lot of different age groups,” Stiller argued in a talk with Entertainment Weekly in 1994. "This Generation X nomenclature has such a negative connotation."

Still, Reality Bites ended up becoming something bigger, anyway – thanks to a note-perfect sensibility which can be traced back to its screenplay. A then-20-year-old Helen Childress wrote it while still in school at the University of Southern California, giving the film an attitude and a direction it initially lacked. "At the time there was no 'Generation X,' Childress told Public Radio International in 2019. "It was called the 'Baby Busters.' And so for a long time this was called 'The Untitled Baby Buster Project.'"

Watch the 'Den of Slack' Scene from 'Reality Bites'

Inspiration would strike, like lightning, out of the blue. For instance, Hawke improvised a scene where he recites the poem "Marriage" by Gregory Corso while playing the guitar. Then there was Loeb's song.

"We had a cassette of Lisa's music and when Atlantic Records wouldn't let the Lemonheads give us a song – [even though] Evan Dando is in the movie – all of a sudden, we moved the Posies up to first end title and we had an opening for second end title," Sher told Uproxx. "And we said, 'Hey, why don't we put Ethan's friend, Lisa, in there?'

Loeb was said to have been the first unsigned artist to ever top the Billboard Hot 100. She went from being nobody to bankable entity in the blink of a kooky glasses-wearing eye. "I gained commercial success [early on]," Loeb told the News Times in 2005, and "it gave me a lot of creative freedom because I made the record before I was working with the major label. So, because I was able to make it on my own with my band and a producer, there's a little bit more trust there that I can make whatever I want, you know?"

Uncertainty kept turning into something more concrete, both for the project and for its characters – as illustrated by Lelaina's canny save ("I don't know") after getting lost among her prepared remarks at graduation. At one point, Garofalo was fired. Initial box-office receipts were underwhelming, before Reality Bites eventually became a lingering cult favorite. Nothing came easy, and that reflects the age in which they lived, too.

"It's funny what ends up striking a note with people," Childress told PRI. "I think it was the fact that we were the people we were making the movie about. There was not that much separation between what the script was and what we were all going through at that time."